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Eicosapentaenoic acid geometrical isomer artifacts in heated fish oil esters

  • Surfactants & Detergents Technical
  • Published:
Journal of the American Oil Chemists’ Society

Abstract

Gas liquid chromatography (GLC) on polar capillary columns showed that the ester of eicosapentaenoic acid (EPA) in distilled fish oil methyl and ethyl esters sometimes is accompanied by several artifacts. The same EPA artifacts did not arise from saponification and/or esterification but were formed in a significantly high yield during prolonged heating of the authentic acid. Physicochemical studies, isolation and partial degradation showed that these artifacts are mainly geometrical (cis-trans) isomers of the naturalcis ethylenic bonds of eicosapentaenoic acid. Several C20 mono-and diethylenic geometrical isomers were prepared and the GLC equivalent chain length values determined. On the basis of measured and calculated equivalent chain length values on two different GLC phases, some of the EPA artifacts were identified as 20:5-Δrans-5,cis-8,cis-11,cis-14,cis-17; 20:5-Δcis-5,trans-8,cis-11,cis-14,cis-17; and 20:5-Δcis-5,cis8,cis-11,cis-14,trans-17. No evidence was found for any positional isomers.

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Author notes

  1. R. C. Wijesundera

    Present address: Ceylon Institute of Scientific and Industrial Research, P.O. Box 787, Colombo, Sri Lanka

  2. W. M. N. Ratnayake

    Present address: Sir Frederick G Banting Research Centre, Food Directorate, Health and Welfare Canada, Tunney's Pasture, K1A OL2, Ottawa, Ontario, Canada

Authors and Affiliations

  1. Canadian Institute of Fisheries Technology, Technical University of Nova Scotia, P.O. Box 1000, B3J2X4, Halifax, Nova Scotia, Canada

    R. C. Wijesundera, W. M. N. Ratnayake & R. G. Ackman

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  1. R. C. Wijesundera
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  2. W. M. N. Ratnayake
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  3. R. G. Ackman
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Wijesundera, R.C., Ratnayake, W.M.N. & Ackman, R.G. Eicosapentaenoic acid geometrical isomer artifacts in heated fish oil esters. J Am Oil Chem Soc 66, 1822–1830 (1989). https://doi.org/10.1007/BF02660756

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  • DOI: https://doi.org/10.1007/BF02660756

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